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Cheap flights from New York to Chicago from $140

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 30/8. Fares are subject to change and may not be available on all flights or dates of travel.
NYC — CHI
27 Aug — 3 Sep1
1 adult

Cheapflights Tip: The best prices from New York to Chicago are usually found in September or January, booked 35 days in advance, depart on a Saturday or Tuesday and return on a Tuesday

Cheap flight deals from New York to Chicago

Discover tips and strategies to find the most affordable flight options for your journey from New York (NYC) to Chicago (CHI). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated 22 August 2025.

Round-trip from

$275

One-way from

$140

Popular in

June

Cheapest in

September

Average price

$419

Good one-way deal

$154 or less
United Airlines
  • United Airlines
  • 18/9-22/9
  • Nonstop
  • 5h 00m total
  • New York to Chicago
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United Airlines
  • United Airlines
  • 30/8
  • Nonstop
  • 2h 41m total
  • New York to Chicago
Search Deals
Highest demand for flights based on searches. 11% potential increase in price ($76 potential increase over avg. return price).
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Cheapest flight prices on average. 1% potential price decrease ($11 potential savings vs. average return price).
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Average for round-trip flights in August 2025
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Price to beat on a one-way flight from New York (NYC) to Chicago (CHI).
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Find flight deals from New York to Chicago

Cheapest flights from New York to Chicago
Explore the most affordable flight options available from New York to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on 22 August 2025.

Thu 18/907:00EWR - ORD
Nonstop2h 38mUnited Airlines
Thu 25/921:23ORD - EWR
Nonstop2h 22mUnited Airlines
Deal found 20/8$275
Sat 30/818:35EWR - ORD
1 stop6h 21mDelta
Wed 3/907:05ORD - EWR
1 stop6h 19mDelta
Deal found 21/8$277
Sun 28/906:10EWR - ORD
1 stop12h 29mSpirit Airlines
Thu 2/1012:05ORD - EWR
1 stop10h 01mSpirit Airlines
Deal found 21/8$280
Thu 4/912:10EWR - ORD
1 stop5h 18mDelta
Mon 8/918:00ORD - EWR
1 stop5h 44mDelta
Deal found 21/8$283
Thu 27/1114:30EWR - ORD
1 stop5h 26mDelta
Tue 2/1208:55ORD - EWR
1 stop5h 58mDelta
Deal found 21/8$285
Wed 8/1006:00EWR - ORD
1 stop4h 23mDelta
Tue 14/1008:55ORD - EWR
1 stop6h 03mDelta
Deal found 20/8$291
Tue 26/805:55EWR - ORD
1 stop8h 38mFrontier
Wed 27/814:40ORD - EWR
1 stop8h 33mFrontier
Deal found 20/8$293
Sun 12/1006:30EWR - ORD
Nonstop2h 38mUnited Airlines
Thu 16/1006:00ORD - EWR
Nonstop2h 15mUnited Airlines
Deal found 21/8$296
Wed 10/921:44EWR - ORD
Nonstop2h 41mUnited Airlines
Sun 14/906:00ORD - EWR
Nonstop2h 15mUnited Airlines
Deal found 20/8$297
Thu 4/906:00EWR - ORD
Nonstop2h 38mUnited Airlines
Thu 4/910:35ORD - EWR
Nonstop2h 17mUnited Airlines
Deal found 21/8$299
Mon 8/921:44EWR - ORD
Nonstop2h 41mUnited Airlines
Thu 11/921:08ORD - EWR
Nonstop2h 22mUnited Airlines
Deal found 20/8$302
Sat 6/911:29EWR - ORD
Nonstop2h 38mUnited Airlines
Sun 7/919:35ORD - EWR
Nonstop2h 24mUnited Airlines
Deal found 21/8$304

Cheapflights Fare Finder

 
Customise your flight search to find flights from New York to Chicago that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 647,157 searches. Data last updated 22 August 2025.
Use the filters below to find and compare flights from New York to Chicago that are best for you.

Fly from

New York

Fly to

Chicago

Route

Depart

Return

Price

NewarkChicago

EWR - ORD

EWRORD

Newark

Fri 14/11

21:59-23:34

Nonstop2h 35m

Chicago O'Hare Intl

Sun 16/11

07:15-10:25

Nonstop2h 10m

$275

NewarkChicago

EWR - ORD

EWRORD

Newark

Wed 3/9

21:44-23:25

Nonstop2h 41m

Chicago O'Hare Intl

Sun 7/9

06:00-09:15

Nonstop2h 15m

$275

NewarkChicago

EWR - ORD

EWRORD

Newark

Fri 5/9

20:15-21:56

Nonstop2h 41m

Chicago O'Hare Intl

Sun 7/9

07:10-10:28

Nonstop2h 18m

$275

NewarkChicago

EWR - ORD

EWRORD

Newark

Sat 1/11

14:45-16:24

Nonstop2h 39m

Chicago O'Hare Intl

Sun 16/11

07:15-10:25

Nonstop2h 10m

$275

NewarkChicago

EWR - ORD

EWRORD

Newark

Thu 18/9

07:00-08:38

Nonstop2h 38m

Chicago O'Hare Intl

Thu 25/9

21:23-00:45

Nonstop2h 22m

$275

NewarkChicago

EWR - ORD

EWRORD

Newark

Fri 12/9

21:44-23:25

Nonstop2h 41m

Chicago O'Hare Intl

Sun 16/11

07:15-10:25

Nonstop2h 10m

$275

NewarkChicago

EWR - ORD

EWRORD

Newark

Thu 18/9

07:00-08:38

Nonstop2h 38m

Chicago O'Hare Intl

Fri 19/9

21:08-00:30

Nonstop2h 22m

$275

NewarkChicago

EWR - ORD

EWRORD

Newark

Thu 9/10

06:10-18:24

1 stop13h 14m

Chicago O'Hare Intl

Sun 12/10

05:05-17:09

1 stop11h 04m

$280

NewarkChicago

EWR - ORD

EWRORD

Newark

Fri 24/10

06:20-18:36

1 stop13h 16m

Chicago O'Hare Intl

Mon 27/10

19:41-09:00

1 stop12h 19m

$280

NewarkChicago

EWR - ORD

EWRORD

Newark

Sun 28/9

06:10-17:39

1 stop12h 29m

Chicago O'Hare Intl

Thu 2/10

12:05-23:06

1 stop10h 01m

$280

Flights are sorted by cheapest return flights first.

Deals found on 21/8

Showing 1-10 of 22 results
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Best time to book a flight from New York to Chicago

Have a flexible travel schedule? Discover the best time to fly to Chicago from New York with our price prediction graph.
Estimated return price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.

Cheapflights Insights

Everything you need to know about your flight from New York to Chicago

How far ahead should I book a flight from New York to Chicago?

Use this chart to determine the optimal time to book a return flight from New York to Chicago. Price data was last updated on 8 August 2025.

The best time to book flights from New York to Chicago is 35 days before your desired departure date. The cost of your flight will likely increase significantly if you book two weeks in advance of your flight.

What is the cheapest time of day to fly from NYC to CHI?

Find hourly flight availability from New York to Chicago. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated 22 August 2025.

When flying from New York to Chicago, the time of day you fly usually plays a role in the price. Save by searching for a flight in the evening, which can drop the price by up to 88% versus a flight at midday.

Weekly flight availability from New York to Chicago

Explore weekly flight availability from New York to Chicago. Discover flights operating on different days of the week, giving you the flexibility to choose a travel day that best fits your plans. Compare info to find the most convenient option for your journey. Data last updated 22 August 2025.

The most flights from NYC to CHI are scheduled on a Thursday (191 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (86 on average).

Related info for your journey

Find useful and relevant information for your journey from New York to Chicago. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • How long is the flight from New York to Chicago?

    Airlines like United Airlines fly from New York to Chicago in about 2h 35m. The time it takes to get you to your destination is usually consistent. New York and Chicago are separated by a distance of 1152 km. Generally, flights for this route are direct.

  • What are the most reliable airlines from New York to Chicago?

    Looking for the most reliable airlines to get you to your destination on time? Our data shows these are most likely to get you from New York to Chicago on time: China Airlines (90%), LATAM Airlines (79%), Iberia (75%).

  • What are the cheapest flights from New York to Chicago?

    The cheapest flight price from New York to Chicago is $132. On average you can expect to pay $184. The most popular route, (Newark - Chicago O'Hare Intl), can usually be booked for $534.

  • Can I find deals for flights from New York to Chicago that include hotel bookings?

    Yes. In addition to deals on New York to Chicago flights, Cheapflights offers holiday packages that include both flights and hotel.

  • How can I find direct flights from New York to Chicago?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from New York to Chicago.

  • Can I find deals for business class flights from New York to Chicago?

    Yes. Cheapflights offers flight deals from New York to Chicago by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

See more FAQs

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

Alternative routes for New York to Chicago

See prices for flight routes from nearby airports that may be better suited for you.
Newark to O'Hare Intl flights

Fly with Cheapflights

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How does Cheapflights help users find flights from New York to Chicago?

Cheapflights makes it easy to find New York to Chicago flights by helping our users search from 900+ travel sites for deals. We also provide you with filters for cabin, price, airline, airports, number of stops, and many more to narrow down that perfect flight.

Why should you use Cheapflights to find cheap flight tickets from New York to Chicago?

Cheapflights helps you find that perfect flight to Chicago from New York by searching from hundreds of airlines and agencies you know and love. We are also free to use, in case you were wondering!

Can Cheapflights find flights from New York to Chicago with no change fees?

Yes, we can. To see specific flights from New York to Chicago with no change fees, users can toggle flexible booking options after using the search form above to find flights.

Can Cheapflights notify me if prices for flights from New York to Chicago become cheaper?

Yes, Cheapflights has a feature called Price Alert, which notifies users when flight prices change. Track prices for your flight to Chicago from New York today and book when prices fit your budget.

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